Sayonara, Zetsubou-Sensei revolves around a very pessimistic high school teacher named Nozomu Itoshiki who, at the very beginning of the series, tries to hang himself on a sakura tree. He is saved by an extremely optimistic student known only as Kafuka Fuura (though in her effort to save his life, she almost kills him). She explains to him that it is simply unimaginable that he would hang himself on such a nice day, especially in front of such beautiful trees. She decides to nickname Nozomu "Pink Supervisor" (桃色係長,Momoiro Kakarichō), and offers to pay him fifty yen to call him by that nickname. After having enough of the strange Kafuka, Nozomu bolts to the school and starts his homeroom class, but the attempt to escape was in vain as he finds that she is one of his students. Not only that, but Kafuka is just the tip of the iceberg, due to each and every student in his class representing a new personality quirk or bizarre obsession, posing challenges that he must overcome in spite of himself.

Each chapter or episode of the series revolves around a particular aspect of life, Japanese culture, or a common phrase in the Japanese language. Typically, this involves the subject being taken either to its most logical extreme (a discussion of amakudari, the practice of "descending" from the public to the private sector, results in Nozomu "descending" until he reaches his previous life), or taken literally (in Nozomu's family, omiai, normally a meeting between a potential match in an arranged marriage, is instead a marriage made official by eye-contact). On other occasions, Nozomu challenges his students to think about the negative aspects of something usually considered positive. These in-depth, off-kilter analyses (along with the reactions of the students according to their own personality quirks) are usually brought to a head with a punchline based on the overall premise, or more rarely, a non-sequitur gag or piece of fan service.

While ostensibly set in the present day relative to its original serialization, the manga uses a variety of aesthetic tropes that evoke the Taishō period, the relatively liberal period in Japan before the rise of militarism in the Shōwa period. Many aesthetic aspects are meant to evoke Taishō liberalism, Taishō Romanticism (see Japanese literature) and Taishō arts (see Hanshinkan Modernism). This is exemplified by Nozomu and Matoi consistently wearing a kimono and hakama (an obsolete style of Japanese school uniforms in the late 1800s), but is also evident in stylistic choices such as the anachronistic appearance of architecture, vehicles, and technology indicative of the Taishō period. However, the fashion of women typically follows the modern girl trend, which is a break from the Meiji period and signifies the style of the Taishō period.

Chapter titles are oblique references to literature, modified to suit the needs of the chapter. The chapter title pages are drawn to resemble karuta cards, with an illustration in a silhouetted kiri-e style. The anime carries this further through a washed-out, grainy visual style that mimics film, and frequent use of katakana (rather than hiragana) as okurigana. The anime also regularly refers to the date as though Emperor Hirohito were still alive, such that Heisei 20 (the twentieth year of Emperor Akihito's reign, or 2008 by the Gregorian calendar) becomes "Shōwa 83".

The manga series was created by Kōji Kumeta and was serialized in Kodansha's Weekly Shōnen Magazine between 2005 and 2012, spanning a total of 301 chapters released in 30 tankōbon volumes between September 16, 2005 and August 17, 2012.[3] The series has been licensed for an English-language translation by Del Rey Manga,[4] and the first volume was released in February 2009. Del Rey released eight volumes in North America before exiting the manga business in December 2010; as of March 2012, an additional five volumes have been released by Kodansha Comics USA.

The Sayonara, Zetsubou-Senseianime series aired in Japan between July 7 and September 23, 2007 on TV Kanagawa and contains twelve episodes. Directed by Akiyuki Shinbo and animated by Shaft, the anime embellishes the story with abundant references to popular culture, mainly through the seemingly random thoughts that appear written on the chalkboard in classroom scenes. Each episode ends with a still image drawn by one of the manga artists associated with Kōji Kumeta. Media Blasters licensed the first Sayonara, Zetsubou-Sensei anime series in February 2010 and was going to release the first English-subtitled DVD volumes in May 2010,[5] but it was put on hold until 2013 when they dropped the rights to the series.

A special 50-minute DVD summary episode titled Sayonara, Zetsubou-Sensei Jo: Zetsubō Shōjo Senshū(さよなら絶望先生 序〜絶望少女撰集, lit. "Goodbye, Mr. Despair Preface: Despair Girls Collection") was released on January 1, 2008. The DVD consists of seven parts, each of them featuring one of main heroines with several additions to the original TV broadcast version.[6]

"Hito Toshite Jiku ga Bureteiru" is a single by Kenji Ohtsuki featuring Ai Nonaka, Marina Inoue, Yū Kobayashi, Miyuki Sawashiro, and Ryōko Shintani, which was used for the first opening theme of the first series of the anime adaptation. It also included "Gōin ni Mai Yeah", which was used for the second opening theme. It was first released in Japan on August 22, 2007 and was published by King Records. "Zessei Bijin" is a single by Ai Nonaka, Marina Inoue, Yū Kobayashi, and Ryōko Shintani, which was used for the first ending theme of the first series of the anime adaptation. It was first released in Japan on September 26, 2007 and was published by King Records.

The Sayonara, Zetsubou-Sensei Original Soundtrack for the anime adaptation was first released in Japan on October 24, 2007 and was published by King Records. It contains music from the first series, composed by Tomoki Hasegawa, along with the two opening themes and an ending theme. The "Sayonara, Zetsubou-Sensei Character Song Album" was first released in Japan on November 21, 2007 and was published by King Records. It contains character songs sung by the voice actors of the main characters from the anime adaptation.

In October 2007, Shōnen Magazine announced that a second season of the anime would air in January 2008.[7] Titled (Zoku) Sayonara, Zetsubou-Sensei(【俗・】さよなら絶望先生),[8] the season began airing on January 5, 2008 and consisted of thirteen episodes. The title is a pun, as the kanji俗 is a mark used in dictionaries to indicate slang or a vulgarity, and has the same pronunciation as 続, which means 'continuation'.

On July 8, 2008, the production of a set of OVAs titled Goku: Sayonara, Zetsubou-Sensei(獄・さよなら絶望先生) was announced. The first volume was bundled with the limited edition of volume fifteen of the manga as a part of Kodansha's OAD Project and was released on October 17, 2008; and the third volume was released with volume sixteen of the manga on February 17, 2009.[9] The second volume was released as an original video animation on December 10, 2008. Although it is technically the third installment of Sayonara, Zetsubou-Sensei, it was promoted as "Series 2.5."

"Kūsō Rumba" is a single by Kenji Ohtsuki featuring Ai Nonaka (Kafuka), Marina Inoue (Chiri), Yū Kobayashi (Kaere/Kaede), Miyuki Sawashiro (Maria), and Ryōko Shintani (Nami), which was used for the first opening and ending themes of the second series of the anime adaptation. It was first released in Japan on January 23, 2008 and was published by King Records. "Marionette" is a single by Rolly featuring Asuka Tanii, Asami Sanada, Yuko Goto and Miyu Matsuki, which was used for the second ending theme of the second series of the anime adaptation. It was first released in Japan on February 26, 2008 and was published by King Records.

The Zoku Sayonara, Zetsubou-Sensei Original Soundtrack for the anime adaptation was first released in Japan on March 26, 2008 and was published by King Records. It contains music from the second series, composed by Tomoki Hasegawa, along with the opening theme and the three ending themes. The Sayonara, Zetsubou-Sensei Best Album: Zetsubō Daisakkai was first released in Japan on May 14, 2008 and was published by King Records. It contains all opening themes and ending themes from the first and second series along with a few character songs and three brand new songs.

A third full anime series, Zan: Sayonara, Zetsubou-Sensei(懺・さよなら絶望先生, literally Repent: Goodbye, Mr. Despair), began broadcast on July 4, 2009 in Japan.[10] The series is once again animated by Shaft and directed by Akiyuki Shinbo, with the opening and ending themes sung by Ohtsuki and the Zetsubō Girls. The opening theme is "Ringo Mogire Beam!" (林檎もぎれビーム!, "Apple Picking Beam!") and the ending themes are "Zetsubō Restaurant" (絶望レストラン) and "Kurayami Shinjū Sōshisōai" (暗闇心中相思相愛). Like previous series, the opening starts off 'low budget' in the first two episodes, simply going through all the placecards of the previous series, before changing to a fully animated sequence depicting the characters, ancient monuments, and the Space Shuttle Challenger disaster. Each episode begins with an unrelated story presented with a pop-up book, and ends with the "Zetsubou-Sensei Drawing Song".

An OVA series titled Zan: Sayonara, Zetsubou-Sensei Bangaichi(懺・さよなら絶望先生 番外地, literally Repent: Goodbye, Mr. Despair No Man's Land) was announced in August 2009. The first volume was bundled with the limited edition of volume nineteen of the manga and was released on November 17, 2009.[11] Although it is technically the fifth installment of Sayonara, Zetsubou-Sensei, it was promoted as "Series 3.5".

"Ringo Mogire Beam!", a single by Kenji Ohtsuki featuring Ai Nonaka, Marina Inoue, Yū Kobayashi, Miyuki Sawashiro, and Ryōko Shintani, was used for the opening theme of the third series of the anime adaptation. It was first released in Japan on July 23, 2009 and was published by King Records. "Zetsubou Restaurant", a single by Yuko Goto, Asami Sanada, Miyu Matsuki and Asuka Tanii, is used as the first ending theme, released on August 5, 2009. "Kurayami Shinjū Sōshisōai" a single by Hiroshi Kamiya was used as the second ending theme and was released on August 26, 2009 by Kings Records.

The Zan Sayonara, Zetsubou-Sensei Original Soundtrack was released in Japan on September 30, 2009 and published by King Records. It contains music from the third series, composed by Tomoki Hasegawa, along with the opening theme and the two ending themes. The Zan Sayonara, Zetsubou-Sensei Character Song album was first released in Japan on October 1, 2009 and was published by King Records. It contains character songs sung by the voice actors of the main characters from the anime.

An Internet radio show titled Sayonara Zetsubō Hōsō(さよなら絶望放送,lit. Goodbye Despair Broadcast), produced by Frontier Works organized by Hirotaka Tahara and directed by Futoshi Satō, began airing on August 28, 2007 on Animate TV. The show is co-hosted by Hiroshi Kamiya and Ryōko Shintani who played Nozomu Itoshiki and Nami Hitō respectively in the anime. Each episode started with a mini drama between Nozomu and Nami then followed by corners replying mails from listeners in several theme related to the series.[12] The show is often referred as SZBH because of the in-show call sign. As of the 180th episode, the show has received over 153,000 mails.

The show features six special broadcast. The first one was aired on November 27, 2007 titled Tokimeki Nāmin Night(ときめきナーミンナイト (TMNN)) which acts as if Ryōko Shintani is a sole host with Hiroshi Kamiya as a guest. The second and third were aired as the second and third season breakthrough commemoration on February 26, 2008 and May 27, 2008 which respectively titled Sayonara Zetsubō Hōsō Senshū: Nyo(さよなら絶望放送撰集・如) and Let's Lilycure Radio(Let's リリキュラジオ! (LLLR)). The fourth special broadcast titled Toki wo Kakeru Radio(時をかけるラジオ) was aired on November 24, 2008 and featured several still image of the in-show character, Sanosuke, marathoning from Kodansha office to the recording studio. The fifth special broadcast was aired on December 31, 2008 and titled Botsu: Sayonara Zetsubō Hōsō(没・さよなら絶望放送). The sixth one was aired on April 15, 2009, titled The Kamiya Hiroshi Show(ザ・神谷浩史ショー,call sign: TKHS).

A special radio event titled Zoku Sayonara Zetsubō Hōsō: SZBH Kaizokuban(賊・さよなら絶望放送～SZBH海賊盤) was held on March 18, 2008 featuring Yū Kobayashi, who plays Kaere Kimura, with Kenji Ōtsuki and Narasaki as guests. The recording of the event was released later as the third DJCD volume. A second radio event titled Kōkai Rokuon Event: Hibiya Kōen Dai-Ongakudō: Yaon(後悔録音イベント≪日比谷公園大音楽堂〜谷怨〜≫) was held on March 24, 2009, featuring Ai Nonaka and Takahiro Mizushima, who play Kafuka Fuura and Jun Kudō, respectively. The recording of this event was released as the ninth DJCD. A total of 21 CDs for the show have been released by King Records. Ten of the CDs contain newly recorded episodes, while the fifth and sixth CDs are the collections of the popular episodes.